Caribbean Vacation Deals

In the Caribbean, you can hike through national parks and scuba dive along underwater mountains. But perhaps your idea of the perfect island vacation is to plunk yourself down on the sands with a frosted drink in hand. The Caribbean has something for everyone.

Want more options? See all Caribbean Vacation Packages.

$200 OFF 5-night vacations

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

Serene palm trees and beach, Punta Cana, Caribbean
Serene palm trees and beach, Punta Cana, Caribbean
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Sandals Ochi Beach Resort

$200 OFF Caribbean Vacations

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Jamaica, Ocho Rios

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

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Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Princess Senses The Mangrove
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$200 OFF Caribbean Vacations

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Green Island

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Couples Swept Away
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$200 OFF Caribbean Vacations

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Jamaica, Negril

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Riu Palace Aquarelle
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$200 OFF Caribbean Vacations

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Jamaica, Trelawny

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Royalton Hideaway Blue Waters, An Autograph Collection All-Inclusive Resort
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$200 OFF Caribbean Vacations

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Jamaica, Trelawny

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Riu Palace Aruba
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$200 OFF Caribbean Vacations

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Aruba

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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JOIA Aruba by Iberostar
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$200 OFF Caribbean Vacations

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Aruba

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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The St. Regis Bermuda Resort
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$200 OFF Caribbean Vacations

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Bermuda

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property
Property
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Sandals Royal Bahamian Spa Resort & Offshore Island

$200 OFF Caribbean Vacations

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Cable Beach, Bahamas

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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The Royal at Atlantis
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$200 OFF Caribbean Vacations

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Paradise Island, Bahamas

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Exterior
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Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Sandals Royal Barbados

$200 OFF Caribbean Vacations

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Barbados

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

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    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property
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Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.
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Waves Hotel & Spa, An Autograph Collection Hotel
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$200 OFF Caribbean Vacations

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Barbados

Book from 09/14/26 to 11/08/26, travel from 09/14/26 to 06/30/27

  • check-small icon

    $200 OFF 5-night vacations

Book this deal View hotel arrow-right icon
Property View
Property View
Minimum stay of 5 nights or longer at a participating hotel or resort and round-trip air required. Savings is per booking and taken at time of booking. Not valid for contracted groups. This entire offer is based on availability and can be modified or closed out at any time.

You will be transferred to our traditional site.

We are currently working on enhancements to this part of our website. A new version will be available soon. Don’t worry – switching over will not interrupt your booking.

Welcome to the all-new Pleasant Holidays booking experience !

You can now plan your next vacation with our exciting new booking engine. Some advanced features are still being developed, and selecting these options may require you to return to our traditional booking experience. Don’t worry – switching over will not interrupt your booking.

We've updated your online experience to make sure you can get your dream vacation. Since our makeover is still in progress, you may experience shifts from our traditional booking experience to our new one.

Are you a travel agent ? We are also working on a new digital experience specifically for travel professionals and we can’t wait for you to see it. Until then, please continue to use the traditional experience here: Pleasantagent.com.

You are a travel agent? Go to Pleasantagent.com. and enjoy the optimized experience for travel professionals.

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Call 1-800-742-9244
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